Process of nitrating quebrachitol



Patented June 12, 1934 or ies i digi i li Charles E. Burke and Russell McGill, Wilmington, Del, assignors to E. I. du Pont de Nemours & Company, Wilmington, Del, a corporation of Delaware No Drawing. Application August 36 1930, Serial No. 479,079

1 Claim.

This invention relates to new explosives and more particularly to an explosive compound produced by the nitration of quebrachitol, and also the method of producing an explosive compound of this type. This invention also relates to explosive compounds containing in combination nitrated quebrachitol and nitrated polyhydric alcohols.

Quebrachitol (otherwise known as monomethyl cyclohexanehexol or methyl ether of inositol) is a compound having the formula CsHeOCI-l'3(OH)s, and occurs in appreciable quantities in rubber latex and at the present time is mostly discarded in solution in the serum after the rubber has been precipitated. It contains five hyi we have found that under proper conditions pracdifficult procedure.

tically all of these groups can be nitrated, giving a compound which possesses excellent explosive properties.

On treating quebrachitol with nitrating acids, we have found that partial nitration may be eiiected with comparative ease, but that complete nitration can only be obtained by much more We have found, however, that under proper conditions approximately complete nitration can be obtained and compounds showing a nitrogen value of from 95 to 100 per cent of the theoretical may be effected by our method.

While it will be apparent from this disclosure that quebrachitol pentanitrate may be prepared in various ways, we have found the following to be a preferred method, although it is to be understood that our invention is not limited thereto:

grams of finely ground quebrachitol is added slowly to 40 grams of 95% nitric acid, the temperature during this addition being maintained at approximately 10 C. 4. 0 grams of concentrated sulfuric acid is then added to the nitric acid solution at such a rate that the temperature rises gradually to approximately 25 C., where it is maintained until all of the sulfuric acid has been added, after which it is agitated for one hour at approximately 25 C. in order to complete the nitration. The product is then allowed toseparate from the spent acid and washed, neutralized and dried in the usual way.

,By this process a product has been obtained hav- (Gl. 260-l42) ing a nitrogen content only slightly below that of theory.

Quebra-chitol pentanitrate prepared as above is a transparent viscous oil which is practically insoluble in water and spent acid. It is quite stable, and the sensitivity as determined by the drop test is somewhat less than one-half that of nitroglycerin.

In cases where quebrachitol pentanitrate can be used in combination with another ingredient in which it is soluble, the nitration can be con-' siderably simplified by first mixing the ingredients and then nitrating the mixture. For example, a mixture of 25 grams of quebrachitol and 25 grams of ethylene glycol has been nitrated by adding the mixture to a slight excess of a mixed acid consisting of approximately 45% nitric and sulfuric acid, at ill-15 C. In this nitration satisfactory results have been obtained by adding the mixture to the mixed acid in the course of half an hour, then agitating for an additional hour in order to complete the nitration. After the nitration is complete, the product is allowed to separate from the spent acid, and washed and neutralized in the usual way. This procedure gives a solution of quebrachitol pentanitrate in ethylene glycol dinitrate which is quite satisfactory for many purposes.

As an example of the way in which either quebrachitol pentanitrate alone or mixtures of this material with other ingredients, as mentioned above, can be used in the manufacture of propellent powders, the following illustration is given:

Parts Nitrocellulose Mixed quebraohitol pentanitrate and ethylene glycol dinitrate 40 Diphenylamine 1 The nitrocellulose may be colloided by the other ingredients, using a volatile solvent if necessary and the powder finished by any of the procedures customarily used.

Mixtures of quebrachitol and glycerol may be a) tion is admirably suited for the preparation of low freezing dynamites.

As illustrative of one embodiment of curinvention, and without in any way limiting it thereto, the following examples of compositions of low freezing dynamites are given:

1. A non-gelatinous dynamite.

Per cent Nitroglycerin 34 Nitrated quebrachitol Sodium nitrate Wood pulp Sawdust Calcium carbonate or carbonaceous combustible 12 2. A gelatinous dynamite.

' Per cent Nitroglycerin 2 Nitrated quebrachitol Nitrocotton Sodium nitrate How lhis invention also contemplates the nitration of quantities of quebrachitol together with soluor carbonaceous combustible 13 'tions of carbohydrates and polyhydroxy alcohols ample, mannitol, sorbitol, dulcitol, ramnitol, arabitol, xylitol;pentaerythritol, erythritol, and other similar compounds maybe used, although We preferably use sorbitol, or xylitol, or both in combination. Mixtures of any two, or of all these compounds may also be used with good results. A mixture of carbohydrate and hydrogenated carbohydrate aids in further lowering the freezing point of the finished explosive product.

The various compounds proposed in the foregoing may also be nitrated separately and then combined, although we have found it most desirable to combine the compounds before nitration.

By the term polyhydroxy alcohols having from four to six carbon atoms we purpose to include the sugars and also the 'polyglycerines and polyglycols.

It will be apparent from the foregoing that various embodiments of our invention exist and W may be practiced within the scope thereof, and 

